Acetic Acid → HCID 71294177, compound

HRID 1484390Notes

Reaction equation

HRID 1484390 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].N1CCCC1.[C:16]([OH:19])(=O)[CH3:17].[OH:20][CH2:21][C:22]1C=CO[C:23]=1[CH:24]=O>>[OH:20][CH2:21][C:22]1[O:19][C:16](/[CH:17]=[CH:6]/[C:4](=[O:5])[CH2:3][CH2:2][C:1]([O:8][CH2:9][CH3:10])=[O:7])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 10883Ethyl levulinateHCID 31268PyrrolidineHCID 16730373HCID 16730373, compound

Product 1

HCID 71294177HCID 71294177, compoundYield 429%

Procedure

11.3 mL of ethyl levulinate (79.2 mmol) was placed in a ground glass single necked, 24/40, round bottom flask and stirring was begun. This was then chilled with an ice bath. In air, the pyrrolidine (1.25 mL, 15.8 mmol) and acetic acid (0.91 mL, 15.8 mmol) was then added. Hydroxymethyl furfural (HMF) (10.01 g, 79.2 mmol) was then added and solution darkened. The cooling bath was then removed and the solution was stirred at ambient temperature until the reaction was complete (by 1H and 13C NMR). The reaction was then purified by silica gel chromatography (using an ethyl acetate/hexane gradient). 17.1 g of product was obtained (85%). δH(CDCl3) 1.21 (t, J=7 Hz, 3H), 2.60 (t, J=6.6 Hz, 2H), 2.86 (t, J=6.6 Hz, 2H), 4.09 (q, J=7 Hz, 2H), 4.56 (s, 2H), 6.19 (m, 1H), 6.56 (m, 2H), 7.25 (m, 1H). δ13C (CDCl3) 197.6, 172.6, 157.1, 150.0, 128.6, 120.0, 116.7, 109.8, 60.3, 56.8, 35.1, 27.8, 13.6.

Workup

  1. temperatureThis was then chilled with an ice bath
  2. customThe cooling bath was then removed
  3. stirringthe solution was stirred at ambient temperature until the reaction
  4. customThe reaction was then purified by silica gel chromatography (

Sources & evidence

ORD record
ord-2287a5252c8f49ceb1e7af8057c5d9d4
Source dataset
uspto-grants-2016_08
Patent number
US09422207B2

Reaction notes

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